Azo triphenylmethane dye.



ARTHUR HAU'SDGRFER, 0F ELBERFELD, AND CARL HEIDENREICH, 0F LEVERKUSEN,

GERMANY, ASSIGNORS T0 FARBENFABRIKEN VORM. FRIEDR. BAYER &,CO., OF

ELIBERFELD, GERMANY, A CORPORATION OF GERMANY.

AZO 'IRIPHENYLMETHANE DYE.

No Drawing.

Specification of Letters Patent.

Application filed May 24, 1910. Serial N0. 563,045.

Patented Jan. 3, 1911.

To all whom it may concern:

Be it known that we, ARTHUR Hnnsnonrun and CARL HEInENnEIcH, doctors of philosophy, chemists, citizens of the German Em- 5 1Ie, residing, respectively, at Elberfeld and everkusen, Germany, have invented new and useful'lmprovements in Azo Triphenylmethane Dyes, of which-the following is a specification.

Our invention relates to the manufacture and production of new azotriphenylmethane dyestuffs which can be chromed after dyeing. The process for their production consists in condensing 'aminobenzaldehydes with two 0 molecules ofan aromatic oxycarboxylic acid,

diazotizing the resulting leuco compounds, combining the diazo compounds with azodyestufl' components and oxidizin the leucoazo dyestuffs, or oxidizing the leuco compounds before or after the diazotation and combining them with azo dyestufi' components.

The new dyestuffs are in the shape of the free carboxylic acids after being dried and pulverized red to black .powders which are soluble in caustic soda lye with a reddish to violet color and which are soluble in con centrated sulfuric acid generally with a reddish color; yielding upon treatment with stannous chlorid and hydrochloric acid a dyestuff of the triphenylmethane series derived from an aminobenzaldehyde and an aromatic oxycarboxylic-acid and an amino compound. The dyes thus obtained dye wool from acid baths from yellow to red shades;

green to dark violet to black shades fast to potting being obtained on chroming.

In order to illustrate the new process more fully the following example is given, the parts being by weight 45 parts of the leuco compound obtained from 1 molecule of ortho-chloro-meta-aminobenzaldehyde and 2 molecules of ortho-cresotinic acid are stirred up with 400 parts of water, 14 parts'of calcined sodium carbonate are added" to obtain a solution and the leuco compound is recipitated again b addin a mixture 0 63 parts of hydroch oric aci 19 B. and 300 parts of ice. It is then diazotized by means of a solution of 6.9 parts of sodium nitrate in water at a temperature of 510 C. The diazo compound thus obtained is introduced into a well cooled solution of 15.5 partsof ortho-cresotinic acid in 500 parts of water and 27 parts of calcined sodium carbonate, 40 parts of a 30 per cent. caustic soda lye are added while the solution is stirred until the combination is complete. It is then warmed to 60 C., the dye is precipitated with hydrochloric acid, filtered off, washed and dried. It is a yellow product scarcely'soluble in water and in dilute acids, easily soluble in dilute alkalies with a yellow color.

To produce the coloring matter the leuco compound is dried and (50 parts of it are dissolved in 300 parts of concentrated sulfuric acid and to this solution while being stirred 7 parts of sodium nitrite in 100 )arts of concentrated sulfuric acid are a ded. The mixture is then warmed to 50 to 60 C. until the quantity of the color does no longer increase. The dark red'melt is poured on ice, the precipitate is filtered off and dried. The new dye 1s a red powder scarcel soluble in water and soluble in dilute alka ies with a yellowish-brown coloration. It dyes wool from acid baths ellow-brown shades which on being treated with bichromate change into a full yellowish-green fast to fulling, potting and li ht. Upon treatment 'ltl stannous chlori split up, the dyestufl' of the triphenylmethane series derived from meta-aminoortho-chloro-benzaldehyde (dyeing wool blue after chroming) and ortho-cresotinic acid and para-amino-cresotinic acid are obtained.

and hydrochloric acid it is Other aldehydes may be used, such as orthochloro-para-aminobenzaldehyde, meta aminobenzaldehyde-ortho-sulfonic acid,' paraaminobenzaldehyde-ortho-sulfonic acid and other azo dyestufl' components, such as alpha nap'hthol beta naphthol, a lpha oxynaphthoic aci beta-oxynaphthoic acid, 1- phenyl-3-methyl-5-pyrazolone,alpha-methylindol, 2-phenylamm0-5-naphthol-7-sulfomc acid, etc. We claim 2- 1. The herein described new dyestuffs obtainable by reacting with the diazo compounds of the triphenylmethane leuco compounds derived from an aminobenzalde-- hyde and an aromatic oxycarboxylic acid upon an azo dyestutf component and oxidizing the leuco compounds, which dyestufisare in the shape of the free carboxyllc acids, after being dried and pulverized red to black powders which are soluble ,in caustic soda lye with a reddish to violet color and WlllCh are soluble in concentrated sulfuric acid with a reddish color; yielding upon treatment with stannous chlorid and hydrochloric acid a dyestuff of the triphenyimethane series derived from an aminobenzaldehyde and an argomatic oXy-carboxylic acid and an amino compound; dyeing wool from acid baths yellow to red shades, green to dark violet to black shades fast to otting being obtained on chroming, substantially as described. k

2. The herein described new dyestufi obtainable by reacting with the diazo com- I pound of the triphenylmethane leuco compound derived from ortho-chloro-metaamino-benzaldehyde and ortho-cresotinic acid upon ortho-cresotinic acid and oxidizing the leuco compound, which dyestufl' is in the shape of the free carbon lic acid after being dried and pulverize a red powder scarcely soluble in water and soluble in dilute alkalies with a yellowishbrown coloration; yielding upon treatment with 'stannous chlorid and hydrochloric acid the dyestufl of the triphenylmethane series derived from Ineta-aminoorthochloro-benzaldehyde and ortho-cresotinic acid and para-amino-cresotinic acid; dyeing wool from acid bathsv yellow-brown shades V which on bein treated with bichromate change into a 111 yellowish-green fast to fulling," potting and light, substantially as described. I

In testimony whereof we have hereunto set our vhands in the presence of two subscribing witnesses.

ARTHUR HAUSDQRFER.

CARL HEIDENREICH.

. Witnesses:

O'r'ro Komo, Cmas. J, WRIGHT. 

